How to Find a Job You Love in Tech

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Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

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Being unhappy with your job is pretty much a given these days. That’s why everyone posts those stupid memes about how bad Mondays are.

A cat meme about Mondays || to illustrate how much people hate their jobs but you can find a job you love

A recent study found that over half of all US workers were unhappy with their career. But why are we so content to stay and do work we hate for a company we don’t like?

The truth is it’s not impossible to find a job you love at a company you enjoy being a part of. But, to get there you might to go down a bit of a non-traditional career path.

Finding a Job You Love

This week’s episode of the Self-Made Web Designer podcast is all about figuring out how to end up in a job that you’re actually excited about getting out of bed for in the morning.

I interview Mr. Kyle Wai Lin. Kyle has made a lot of career transitions. He was a tv producer. He started an agency. He started a magazine. But, then he went on to become a creative director at a tech startup called Tempo.

Along the journey Kyle found what it takes to have a job that you love.

Hint: it’s a lot less about money and position than you think.

In fact, some of the most important questions you should ask are

  1. Does this company align with my own values?
  2. Do I like the people that I’ll be working with?

Finding a job you love is not a fairytale. It is possible!

Check out this episode to see how Kyle did it and you can too.

You’ll Learn

  • How to know which career path is right for you in tech
  • Why the people you work with play a huge factor in how happy you are in your web design career
  • How to know if you’ll fit in well with the culture of a company
  • Why learning and experiencing things outside of your job is important to your web design career development
  • The intrinsic things everyone should have to be a good web designer
  • How to know when it’s time to pivot careers as a web designer
  • How to know whether you should work for a company or on your own
  • The role failure plays in your optimum career
  • The role diversity plays in your web design career
  • How to manage up as a web designer
  • The role your personality plays in success and fulfillment in your web design career


Chris: [00:00:00] A recent study found that over half of all U.S. workers are unhappy in their job. Over half! Think about that number. That's a crazy amount of people who are content to stay in jobs they hate for some silly reason. Like some unwritten rule that you've got to stay at a company for a certain amount of time, or it'll look bad on a resume.

Or maybe it's fear. Maybe it's the fear of, if you go out and get another job, maybe it's going to be worse than the job you have right now. And so better just to stay put and do with it because work is supposed to suck. Right?

This week's guests went a nontraditional route to ultimately finding a position he loves at a company. Actually enjoys being a part of, and that is exactly what we are talking about in this week's episode.
Hey, I want to welcome you to the self-made web designer podcast. If you are new to the podcast, I want to say, I'm glad that you're here. If you've been here for a while, you know, let's do our traditional internet high five.

Ready? One, two, three, go. Okay. I hope you air high fived me at the same time or I was air high-fiving myself and that's no fun. Hey, want to encourage you to take a second, if you haven't already subscribed to the show, leave us a rating, leave us a comment and invite some friends to listen along because it's always more fun to do things with friends.

Our guest this week is the one and only Mr. Kyle Wai Lin. And Kyle has a bunch of different experiences doing a bunch of different things at different jobs in the tech world. He was a production assistant.

He started his own agency and he ultimately ended up. Landing a position as a creative live director at a startup in Silicon Valley, doing a lot of awesome things in the tech industry and Kyle shares with us, all the things he learned from his journey of pivoting his career.

Over and over again, reinventing himself. Trying new things out. Not settling for the status quo. And ultimately he shows you how you can find a job that you love. Being able to get up and get out of bed to go to in the morning. It's a fantastic episode with a lot of good insights. Are you ready for Mr. Kyle Wai Lin? All right, here we go.

Well, Hey Kyle, thanks so much for being on the self-made web designer podcast.

Kyle: [00:02:57] Awesome. No, thanks for having me, Chris. I appreciate it.

Chris: [00:03:00] Yeah. So tell us a little bit about who you are and the journey to where you were and how you got to where you are today.

Kyle: [00:03:09] Oh, man, that is a loaded question.

Um, I will try to start from the beginning, but it is not. A linear path. Um, you know, I think I first started off in, in, in, um, advertising. I was working in broadcast production doing like print web TV spots, radio spots as a, as a producer. Um, and, um, you know, I saw what they were doing and that was going to all these shoots and it was cool.

And I'm like, man, like I want to. I want to work on like TV spots and like cool things like print campaign. So, um, I went back to school, um, and got a master's degree at VCU, uh, grand center, great school, shout out to them. And that really set me on the path into, um, advertising design and tech, um, you know, 10 years later or more other, um, I've worked in and out of different tech companies, everything from Apple, the Twitter I've worked at.

Um, you know, every single kind of big ad agency even think of mostly digital, so RGA and QA, um, and then a ton of big and small startups and ad agencies in between. Um, right now I, Oh, and then, and then after that, I, I, my own agency for about Connie, it was like three or four, two or three years, which was quite a ride.

And, uh, most recently I, uh, took up a role as creative director at a fitness tech company called tempo.

Chris: [00:04:29] You know, you've had quite the journey as far as your career and the path that you've taken to get to where you are now. So how would you say you found like the best fit for you or have you found the best fit for you and what are some things for people who have maybe not had that linear journey that.

Most of us aspire to have, like, what would you say would help them to figure out the path they should take or where they should end up?

Kyle: [00:04:57] That's a good question. Um, you know, my, my wife tells me that I make, I tend to make kind of poor decisions when it comes to, um, jobs and careers, um, uh, or maybe jobs, more, more Southern careers, but this is my own personal thing and my wife would not agree, but I would say, you know, um, don't pick a job based on, um, like a title or.

Um, or, or even what the company does, but rather the people that you're working with, and sometimes that'll lead you down really different ask pass. He probably wouldn't have taken and otherwise, but, um, I've done that sometimes I've found the right people. Other times I've found the app, slew wrong people.

That either way it's like you learn even from the wrong people, like you might even learn more from the wrong people than the right people. Um, and then also just straight and yourself with people that you want to be and lead yourself with values. So if you believe in something, um, you know, like myself, I think I've mentioned this to you before.

Uh, diversity is a really big part of my platform and, um, I would never join a company. I would never even work with a client unless I felt that they shared that value.

Chris: [00:05:58] Talk a little bit about that as far as, you know, the, the people aspect, how do you figure out if, if you fit with somebody versus not fitting with somebody and how do you do that?

Just on the basis of like an interview, you know, because I think it's somewhat. Difficult to know like, Oh yeah, me and this company are going to get along. Well, like you might get in there. And then a month from when they hired you, it's a nightmare. So what are some mile markers for you that have like showed you?

Like, okay, this is great. This is a good one.

Kyle: [00:06:28] You know, I think, um, you never know, like you said, sometimes like a month into a job or a project you'll, you'll hate yourself and hate your, every decision you've ever made. But, um, generally speaking for me, and this is a PR like a personal thing, everybody's going to be a little bit different.

I would say. Um, I always go by this kind of rule of thumb that I think of that as, um, can I, I sit next to this person on like a coast to coast air, airplane trip, and like, Have a good talk, have fun, enjoy myself peacefully, quietly, you know, like, am I going to hate them? And they're going to hate me. So that's like one kind of quick rule of thumb.

Um, and then the other bit is probably, I really like people that are able to, um, talk casually, speak very casually about what they do. Versus people that feel like they have to overcompensate or use big words or use jargon or, um, you know, like almost like competitive talking or competitive men's planning.

Like I really, if I see that I'll be like, no, this person is not right. You know, the more casual you are about what you do, the more, um, As at least I see it. The more confidence you have in what you do. And it gives me confidence in you, if you're that casual about it.

Chris: [00:07:38] What I've found like a reoccurring theme on the podcast is how much those soft skills are.

So incredibly important too. Either having a business, owning your own company or, um, building a career in tech. So for, for those who have just devoted themselves to the hard skills, to the design aspects, to, you know, the book studies to whatever, like what's a way that they can grow those soft skills. So they are the kind of person that you would hope to sit next to you on a coast to coast trip.

Kyle: [00:08:14] Yeah. Wow. That's a good one. I mean, the simple answer is just to be human. Like if you have friends. That's probably a good sign. If you don't have friends, maybe that's not a great sign.
Maybe make some, you know, and, and, and spend time with people outside of what you, you do for your like hard skill portion of your career.

Um, you know, family also, I think like if you have one, if you treat your family well, if you know this person's future family, their family, well, That's also a good sign. Um, because you know, nobody's going to treat you any better than they do their family stuff. They either, you know, if they, if they say treat their family terribly, um, then that's probably a bad sign.

Or the other thing too is if somebody, you know, like if you're at a restaurant with somebody and you, you notice that they, and this is a little bit off topic, but they, they treat the waitress or, or busser poorly. Um, you can assume that they're not gonna, you know, this is just how they treat people that are doing anything for them.

And that just kind of red flag. But in terms of developing your soft skills. I mean, man, like just be human, like do things outside of work. Like a lot of things outside of work, you know, um, go on trips, like travel the world, um, you know, have a hobby, nothing to do with what you do. Um, you know, um, just things outside of your space.

And I don't think they teach that in school and you know, it's something that you kind of learn and get more confident with over time. Um, Yeah. So it is challenging. I would say these days I do come across some folks that probably could use better soft skills and even not just that at the beginner level, but even in the advanced stage, I definitely come across people that I'm like, man, like, how have you made it this far?

Um, or maybe you've made it this far because you are ruthless. And I don't know, like for me, that's not a value, um, you know, ruthless, you can, you can be sort of a good person and, and still, um, make it along the way. I like the thing at least.

Yeah. And you've, you've done a fair bit of probably teaching at the college level from what I can remember.

And, um, you know, you, might've already kind of answered this question already, but what kind of things have you seen that have really helped students stand out, especially those who have gone on to be successful in their careers?

I would say the types of students that I think do the best for the ones that.

Um, can figure out anything, like you throw something out that they'd never seen before. They didn't learn in class and we haven't even talked about, um, but they come back and they're like, I figured it out, you know? So this kind of candy attitude, um, to just be, are you able to sort things out for themselves?

I think any employers for that, and yes, we'll do a hard skill if they hire you for design development or whatever. Um, but, but if you can't just figure out how to do XYZ. Um, you know, that that would be a red flag. I would say for any employer.

Chris: [00:11:07] I'm finding a lot of times when, when somebody comes to me for advice from self-made web designer, that there's just certain things that I can help them with.

And certain things that like, like I just can't help them with, like, it has to be something type of internal motivation, some type of insurance value or you know, skill set. And the question that I have been having is can, can I help them with those things? Have I just not figured out how to explain it or how to coach somebody in the right direction.

So has that been your experience as well? And have you maybe figured out the secret sauce of being able to get past those things that are kind of intrinsically necessary?

Kyle: [00:11:48] You know, like I've I found that sometimes it does take a certain personality type that can not be taught. Um, like for example, I started off my career as a producer and I was not a great producer.

Like I was okay. I was pretty good at figuring stuff out now, but, um, but ultimately like after, you know, I think it was like two and a half years of doing that. I said to myself, like, I am probably not the personality type for this. And I think it takes a lot of self-awareness. Yeah. Let's say that. And think that, and you know, in the same, I've seen students in mind from Miami ad school, from, from, from general assembly who, um, may have started off and the design class may have started off in creative class and, um, And down the line, they become a producer or down the line.

They become an account person and account executive, new business person just strategists something different than what they were planning on in school. And I think it just takes a lot of professional maturity and self-awareness to really know, um, You know, if your personality like lands in a place where you can maneuver it into your chosen career path.

And, and, um, I think it's okay to just say, Hey, like maybe this isn't for me. I can still use these skills, but I should probably be doing this other thing that I'm maybe better suited for
Chris: [00:13:04] Let's chat a little bit. Cause you've worked for some big companies. You work for small companies, you've had your own companies.

And I think a lot of times, like there's kind of two paths that people have when they're thinking of having a design or, or tech career. And that's either I'm going to work for Apple or Google or whatever, or I'm going to start my own agency or have my own startup, you know? And so you, you've kind of seen success of both of those things and, you know, have essentially decided like I'm going to do something else.

So maybe, maybe talk about. You know, the ups and downs of that and what ultimately led you to decide to be where you are, right? Yeah.

Kyle: [00:13:42] Yeah. Well, that's a, we could have, like, we could talk all day about that one, man. You know, like I've seen success and failure at big and small places. And sometimes the success had to do with me and in my own, you know, approach to it.

Sometimes it's had to do with outside forces that are beyond my control and, um, Ultimately man, like having worked at Apple, having worked at square, having worked at big agencies, um, you know, I I'm not, and this is a very personal thing. Like it's just not really, um, it doesn't really motivate me to be, um, you know, a cog in the wheel, even at these incredible companies.

You know, some people love that and I think there's a lot of value to that. Like people talk about it when it comes to Apple in, in, in, um, they kind of use the analogy of like, You know, Apple is just full of these samurais that like hone their craft, like, you know, do this very specific point, you know, and they just do this one thing.

So extremely well. And everybody at Apple I would say is like that. And a lot of these big tech companies also. Um, and then there are people like me for who prefer to sort of be a bit more of a generalist who want to have their hands in different pots who enjoy. Um, you know, figuring things out and not really having a process or system like having to create one along the way.

Um, and for me, that's like, that's true creativity, and that's kind of what gets me excited in the morning. Not gonna lie. It also is probably a lot more tiring than then, than fitting into one of these big companies where there's a lot of, um, process, procedure and resources. Um, but for me, like when you have, you know, The less resources you have, the more constraints you have, the more interesting things get.

So, um, that led me to, you know, creating my own agency, um, and, and just working for small clients and kind of figuring it out. And that was actually a lot more rewarding than working on a big campaign or working on a big website, um, because. You know, I had to, I had to just figure it out. Um, and, and then where I'm at right now.

Yeah. And I worked for, um, a fitness tech company called, called tempo. And when I joined the company, it was, I think I was like maybe the 15th employee, you know? So it was still like a really small, early stage startup series, a, you know, we were just kind of figuring it out. We hadn't even had a product out and available to the public.

We haven't had a website where we had like a, like a landing page, not a website and a. You know, in over the past six months, probably in large part because the quarantine, um, we, we blew up, you know, series B funding. Um, we, we, I don't know, quadrupled in size. Like we're probably like 70 people now. Um, and it's becoming like a, I guess like a pretty safe to say a midsize company.

Um, and. It's still really exciting. It's still crazy. Every day is a roller coaster every week to week. I do not know what's happening sometimes or things change so quickly. And for me, I love that kind of challenge because it just makes it. Um, it makes an interesting, you know, um, yeah, so big companies for some people, for me, small companies are, are just more interesting.

Chris: [00:16:50] Yeah. I mean, it's interesting that you say that and it just highlights the fact that it's so important to, to know yourself and, and I think you probably have a better insight into that because. You've you've taken the risks and gone, you know what? I'm not happy here. And so I'm just, I'm just going to go ahead and leave.

And I know there's this kind of standard with companies of like, all right, you've got to stay for this much amount of time and you've got to do this kind of thing, but it sounds like you haven't necessarily bought into that idea. So talk a little bit about that.

Kyle: [00:17:22] Yeah, no, that's a good one. I'm definitely not.

I'm not into it. Like if, yeah, the, I mean, there's this kind of, I don't know what it is like. Standard in everyone's mind and probably in a lot of recruiters line, probably for good reason, uh, that people need to stay one or two years or 10 years at a company in order to have, you know, made an impact or gotten the best out of it or whatever.

But for me, it's like, I am at a company for six months and I'm like, yeah, this, these people do not align with my values. Like I'm not into this. I'm out. Um, you know, uh, or alternatively guide, like if, if, if I don't align with their values and it's pretty obvious, like they'll, they'll kick me out and that's definitely happened too.

And I think, I think you gotta, you gotta just have self-awareness. No, that that's okay. Like better, you spend too much time at a job too. To, to, to allow it to like, you know, suck, suck the, your values from you are having to, um, you know, be opposed to what you believe in.

Chris: [00:18:18] And you mentioned, you know, the, the, the generalists versus people who get really specific in their skill.

And, you know, like I know people from Amazon who, the only thing they do is develop for the buy now button. You know, and I'm like, some people love that idea. I can't imagine a world where I could show up every day to work and work on a button for the rest of my life. You know? So, uh, and it's almost like there's, there's this, this.

Kind of thought process and popular culture when it comes to tech companies, that the more specific you can get on your skillset, the more valuable you are, but you've kind of blocked that mentality. And it sounds like you've not lacked for opportunity. So talk a little bit about that.

Kyle: [00:19:04] Yeah, no, that's a good point.

I would say, um, you gotta, you really gotta find the people that, that need the right people at the right time. So timing is everything. And for me, I found that. If you want to be a generalist, um, if you find like an early stage startup series, a startup series, B startup, those are the kinds of companies you want to probably aim toward because they need generalists.

Chris: [00:19:23] Yeah. That's great. So, you know, you mentioned, um, one of the best things that you've seen in students is just being able to, to figure things out. And also being part of a startup where, you know, you're having to do a lot of things across a, probably a varied amount of fields. You're probably having to do that yourself.

So how did, how do you, how do you go about that for yourself? Like what are the steps to problem solving something you've never seen before?

Kyle: [00:19:49] It depends on the thing, you know, I mean, every day from like a creative standpoint or from a design standpoint, I'm working on something, anything from. A range of sort of like production design to really have these strategic thinking, you know, I'm planning.

Um, and then, and then in addition to that, for my job, there's a layer of sort of, um, planning, you know, projecting like resourcing, um, administrative work, recruiting, like all the things, you know, a lot of Googling I would say is helpful. Like if there's something I literally have never seen before, which happens all the time and like, I think it takes professional maturity to realize that you just, I mean, you know google it, you know, you ask people that, you know, that do it, or have done it or do regularly. Um, and then for me, I just kind of like to dive on in, you know, like even like, I'll definitely be transparent. Like if it's something I do not feel comfortable with or is not something that you should have me do.

I'll raise my hand. I think that's important too, to say, Hey, like maybe we should get somebody who's done, you know, legal into like legal work or something. Cause I, that is not my jurisdiction. But if it's something that I think is within reason of any, a reasonable, smart human, I would say, I just dive in, figure it out, probably make mistakes along the way.

Um, You know, and I'm forgiving, forgiving to myself and making mistakes, and hopefully, you've found somebody to work for or people to work with that are, that are also forgiving about mistakes you might make as you, as you learned.

Chris: [00:21:09] Yeah. And I think that's so important. We've talked about, you know, this idea of self-compassion, a ton on the podcast.

And I think it's so important for growth because there's no growth without risk, you know? And it sounds like you, you haven't been afraid of that. Like afraid of the failure, afraid to get fired, afraid to say, you know what? It's been six months. It's not working out. I'm okay. If we move on, you know? So how do you, how do you foster that in yourself?

Do you have that mindset of like, failure's fine As long as moving forward?

Kyle: [00:21:42] it doesn't ever get. Easier, but you kind of become more used to it, I guess. Um, you know, like there, yeah. Even jobs where I've worked for eight months and I'm like, yeah, this isn't a fit. I'm sorry. And I hope it's okay. You know, no hard feelings, like, I'm sorry if I put you in a bad place.

I mean, I think again, like you just kinda, you just kinda learn over time. It's kind of like any relationship like if you're in a relationship with somebody romantic relationship, we'll say, or even friendship, but any time it takes a lot. To be able to look the other person in the eyes and say, Hey, like this is not working out.

Um, I think I've done that in my, in my life enough to, to know when that moment happens with my career. And, um, you know, when you're dealing with another person when you're dealing with another company or, um, partners or partnership, um, it's never going to be easy, but if you, when you, when you just kinda keep doing, when it, uh, you realize that the value and the importance of doing that.
Uh, cause if anything, if you are feeling that way, um, it might be showing your ability and your work, and it's probably better for the other party as well.

Chris: [00:22:45] Let's talk a little bit about, um, diversity in the workplace. Cause I know that this is an important topic all the time, but it's definitely been highlighted in, in this season.
What types of things have you done to make sure that diversity is fostered in the team you've built?

Kyle: [00:23:03] Yeah. Um, Yep. I mean, one of the most important things, I mean, you can have a diverse team. You can have a diverse looking team or a diverse team on paper, but I think, you know, unless you're, unless you really hear people and listen to what they have to say and allow them to be, to be heard and be seen and project their voices, um, then it doesn't matter how diverse your team is or.

Um, you know, on paper, you really have to like go above and beyond to listen, hear and see people, um, and, and project for them, you know? Cause I think diversity also is not just the way somebody look or their religious beliefs are there. Um, you know, gender identity, but. It's also, you know, things like age or, you know, if somebody is more of an introvert versus extrovert, like their voice will not be heard, you know, or if somebody just has a totally different communication style and sometimes it might even be like an embracive communication style, you know, you wanna, you want to foster, you know, the ability for them to feel comfortable, um, with projecting their own voice, even if, um, you know, it, it can be challenging.

Uh, so yeah, in urgency and in creating space for that too. Cause I feel like I've definitely worked for people who no, I speak a lot about diversity and then don't necessarily create the actual space and room to listen to people too, to give them a voice. And you just gotta. Stop and listen, you know?

Chris: [00:24:29] Yeah. Yeah. That's great. And, and I think, you know, like you mentioned, the root of it is, is needing to make the extra effort because it's, it's almost natural to say that the person is the best fit. For this job as somebody who looks a lot, like me, or enjoys the same things that, that I do, you know, and it almost like we, we talk a lot about the culture and making sure they're a right fit for the culture, which can almost be like code for, you have to have the same exact values that I do.

And so it takes, it takes that extra. Like, let me find somebody that has. Maybe different values, who I wouldn't necessarily be friends with. Um, but would I know no, without a lot of value in a lot of perspective. So, you know, how do you do that? And more importantly, how do you, how do you make sure you convey that upward, you know, to people who you speak to or people who are you're accountable to, you know, as far as in the company that you're working for.

Kyle: [00:25:36] To go back to the, to the sort of, um, coast to coast airplane trip thing, you know, for me, um, you know, a great coast to coast trip with somebody can be with somebody who you totally disagree with, but you have such a great conversation about that disagreement, you know? Um, and I think it's important to, to allow for those kinds of disagreements and discussions and like invite it.
You know, I know with my team right now, I. You know, every Monday morning I'd be with every one of them individually. And then midweek, I check in and at the end of the week, we have kind of a powwow, um, where we just kinda have, you know, updates. And then we have as much time as I possibly can create for open discussion.

Like what do you think about anything? What do you think about this? Please tell me your thoughts on this. Um, and it takes a lot of ex extra effort and time and slows down the processes a little bit for sure. Um, but I think for me, it's like, you have to. You have to take those extra steps and make that effort.

Like we said to, um, you know, in order for, for, for like the long term success, you know, short term, slow long term, you get you aligned values, you hear people, you allow them to speak and listen. Um, and then it just works, you know, in order to the other question, though, in terms of how to sort of manage that up, that's a lot harder, you know, like I'm learning that every day I learn more about it every day.

No magic, managing up, managing vertically and communicating up and horizontally in all directions. Like, um, it's, it's challenging. Like, you know, you can, I'd say the best way to do it. For me, I've found is to kind of lead by example, you know, your leadership style might be different than the person above you or the person to your right and left and, um, and that's okay.

Um, you know, I think the best way to, to, to sort of, you know, Uh, share those values with them is not necessarily by telling them what you're doing, not even, you know, uh, asking if they would do it, but rather just doing it in your own land. And then allowing them to see that what you're doing. Um, yeah.

That's, I don't know if that's been, if that's been successful or not, to be honest, but that's kind of my policy, you know, cause people, nobody likes to, you know, you know, be told anything, nobody likes to, um, you know, for you to like bring it up or flag up those kinds of things. But if you just lead by example, You know, the, the, the proof's in the pudding, I guess you could say,
Chris: [00:28:00] You know, you mentioned diversity in personality and even, you know, hiring somebody that might have an embracive style when you're more of a laid back person.

And, um, you know, I, I, I know I I've struggled with that because, um, I'm definitely more of the direct. Person when it comes to pretty much everything in my life. Um, and so I've, I've had to learn how to, how to temper that personally. But personality is, it can kind of be like a tool. And I think it's a lot more flexible than most of us think, you know?

And so we think that, okay, I've got one personality tool in my tool belt and, and I, and it's a hammer. And so if the situation doesn't yeah, call for a hammer, then I'm either going to make it. Call for a hammer. I'm going to leave, you know? So how do you change that? How do you, how do you navigate it and become flexible and learn from all of those things?

Kyle: [00:28:50] That's a great way to look at it. And what's funny is there are hammers and screwdrivers and tape guns and staple guns and, you know, coffee machines and water bottles. There's like, there's no like, you know, personality types come in, all sorts of shapes and sizes and categories. And, um, Even right now, when I think about my own team, there are some people that are more direct, I'm able to kind of pick up and take projects, move, and then other people that are, um, that slowed down a bit that are a lot more inquisitive and introspective and, and, um, thoughtful, I would say about what they do and, you know, Both both of those, not that those are the only two in the world, but within that spectrum, um, they, they both kind of come with challenges.

And what I like to do as a leader is to, um, try to find the projects and opportunities for the right personality type. Uh, and it could be a project that could also be, you know, on this specific project you're working with. These XYZ stakeholders and those stakeholders appreciate people that are more direct or appreciate somebody who's more thoughtful, inquisitive and, and, and, you know, curious about the way they approach things.

So I try to do that. It's not a perfect science, um, even myself, like I, you know, I try to adapt as much as I possibly can. Um, You know, when I'm dealing with different types of people that respond differently to different, you know, styles and personalities, and I'm not always successful for sure. Um, but, but I like to think that, you know, at least I'm putting in the effort to try,

Chris: I guess, a piggyback question from that would be how have you helped people on your team?

More or less hone their personality. If it's something that is creating a lot of tension in the team to help them, you know, figure out how to work with people who are such opposites, you know, despite having this one set of personality traits. Yeah.

Kyle: That's a great question. I think, and my answer would be, and this is my latest answer.

Cause I think it changes and has changed over the years, um, and shared group of values. So people can be all sorts of things, you know, on the spectrum of, you know, personality when ability skill level. But if everybody has a shared set of values, um, you know, they, they generally believe in the same things and that's kind of what makes the team special and what makes the team work, then it works, you know?

Um, and I'd say when I interview people or when I'm talking to a potential partner, uh, like a vendor even, I just want to make sure that. They're aligned with my values, you know, um, they give space to listen and hear and actually talk and have a conversation with people. Um, it's okay. If their personalities are different, if they come from different place, they come from a different, totally different world.
But as long as they are like genuinely good people and share what I share, then I think there'll be okay.

Cause you can't really, you can't like teach values that they're already kind of taught. They like come as a package, you know? Um, Yeah. I mean, you can, you can definitely, you can definitely like share your values with other folks and they might disagree, but, um, it's hard to sort of change that in somebody.

Cause it's something you're sort of born with and develop over time and that's okay. Um, but it doesn't always work. It's like oil and water on a team or with a partnership. Um,
Chris: [00:32:02] Let's talk a little bit about the agency that you built yourself, you know, because I think there's, there's, there's kind of this romanticized idea of being your own boss and writing your own schedule and being an entrepreneur, you know?

And so, you know, I have certainly found that it's not. It's not awesome all the time. Like, you know, most, most of the time there are nights where you're up late at night and you're not going to be able to sleep because something is going on within the company. So what, what ultimately led you to decide to move away from that?

Kyle: [00:32:37] You know, I might, I might move back caveat. Like I might move back eventually, I think to that, but I will say, like you said, you know, there are nights you're up all night and, um, You know, trying to make it and meet or figure out, uh, you know, solve a problem and it's not easy and it's not for everybody. Um, what made me move back, I think, or away from that, I'd say.

At least for now is, um, you know, I wanted to work with a larger team, kind of, um, have a lot more sort of deeper project access where, you know, working within an agency structure, you know, by the nature of what you do, they hire you to do one thing, you know, for like a six month project you're in and then you're out.

You don't even get to necessarily see the project through you don't need to, you know, and you can get to, you know, help out and update it and iterate on it. And I was looking for that kind of ownership and that kind of ability. And then also I want to just surround myself with more people. That had, you know, kind of cross functional abilities.

Um, my agency was like five people, you know, and then they're very talented people, but I, you know, after doing it for like three years, I was like, man, I, I kinda maybe it's time to dip back into the world, many people and see what that's like. But I still, like I mentioned earlier, I still try to keep it pretty small, just so you can have.

No, um, hopefully deeper relationships

Chris: [00:33:55] So, for the designers who are just getting started or developers or whoever, um, you know, what, what's the best advice that you can give them on their journey.

Kyle: [00:34:05] I would say get weird, you know, try things that you, that you didn't stop set out to try, you know, like definitely have an idea in mind of who you are and, and where you generally want to go.

Um, but take that, that who you are bit the value of it. And then apply it to different companies and situations that you might never have thought you'd land yourself in. Like, for example, you know, you're a designer and you knew you wanted to work at a big agency. Um, and then some strange opportunity just finds itself to you and to work with a company that builds, you know, um, coffins or something, you know?

Um, yeah. I don't know, immediately dark or morbid, but like, no, I don't know, man, like, you know, if it's interesting that people are cool and the values are shared. Try it, you know, it's okay if you, in six months, like, yeah, coffins really aren't my thing. But you might also find a place where, um, your values and skills are, are heard, you know, more than effort because you chose a place that's so small and so niche.

And so, you know, sort of weird. So just keep it create room for just odd decisions and decisions that you might not have.

Chris: [00:35:15] Yeah, that's awesome. Kyle really appreciate you being on the self made web designer podcast. If people are trying to connect with you, where would they go?

Kyle: [00:35:23] Where would they go? Ah, these days probably, I guess like, I'm not that really prolific on Instagram, I guess you could say.
Um, but you can hit me up on Instagram. Uh, my handle is, uh, Kyle Wailin, K Y L E WAI L I N. Um, you can DM me or email me, just I'll put out my email address. My personal email address is a K Y L E W A I L I [email protected]. Mmm. Um, those are both great places. You can also find me on LinkedIn. Um, LinkedIn, I'm pretty active on so you can hit me up there.
Definitely. Yeah. Yeah.

Chris: [00:35:59] Well, Kyle, thanks so much again, hope to have you on again and maybe talk about the agency that you're going to start in in a few years now. You never know.

Kyle: [00:36:07] Join me on that, on that man. I mean, I'm looking for, I would need new partners for that. And you gotta find, you know, I like diversity and you are a supporter of diversity and I can see them that shared values, man.

So let me know when you're ready.

Chris: [00:36:20] Awesome to hear Kyle's perspective on finding a job that you absolutely love in the tech field. And I love the idea that. What you're doing, or the amount of money that you're making is not nearly as important as the people that you are doing the work with the relationships that you are building, whether or not you fit into the culture and would like to hang out with those people, even if you didn't work together at the same company, such a great episode.

Hey, I want to thank you again for being here next week. We've got a, another great. Guest, and it's going to be a fantastic episode. Are you staying up with me Wednesday night at midnight, it is dropping and it's going to be a ton of fun. So until then have a great week. And don't forget if you don't quit, you win.

How to find a job you love || Illustrated by a twisty road because it might take a non-traditional route to get there


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

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